Chestnut Hill Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chestnut Hill Vacation Homes

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Relax in a serene backyard oasis with Adirondack chairs, a table, and a chair, surrounded by a fence.

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (59)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
Surrounded by lush green hills, this serene river landscape offers a tranquil escape.

LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

10.0 out of 10, Exceptional, (238)
"House was clean and a very nice location. "
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
A working horse farm in Southern Lanc Co., nestled in Amish country.
Relax on the deck with a view of the surrounding hills.

A working horse farm in Southern Lanc Co., nestled in Amish country.

2.0 star property
10.0 out of 10, Exceptional, (11)
"Beautiful place , peaceful, just a breathe of fresh air . They were great and responsive "
A working horse farm in Southern Lanc Co., nestled in Amish country.
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!
Relax by the fire pit in a tranquil outdoor setting surrounded by lush greenery and Adirondack chairs.

Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

10.0 out of 10, Exceptional, (251)
"The pictures does no justice to this listing. It was absolutely beautiful and the stay was awesome. The hostbwas kind and generous. We had everything that we needed. Definitely would book again if I am going to be in the area. "
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!
Waters Edge
Equipped with a stainless steel range, microwave, and exhaust hood, this kitchen offers a clean and contemporary look.

Waters Edge

10.0 out of 10, Exceptional, (131)
"Beautiful scenery, Breath of fresh air. Very clean and comfortable. Very modern, we truly enjoyed our stay. Extra over the top amenities was a definite plus."
Waters Edge
The Chalet is located in the woods of a gated property with a covered porch.
Cozy cabin-style room with a kitchenette, sofa, and window offering a forest view.

The Chalet is located in the woods of a gated property with a covered porch.

9.4 out of 10, Exceptional, (22)
"Beautiful little house, great surroundings. We live every minute."
The Chalet is located in the woods of a gated property with a covered porch.
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
Enjoy cooking in this well-equipped kitchen with a large island and oven.

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

9.6 out of 10, Exceptional, (5)
"This property was amazing! My family of six, really enjoyed the pool, large yard, for one including a balcony, toys for the kids, and many more! Will definitely be staying again in the future"
The price is CA $837
CA $1,514 total
includes taxes & fees
Aug 10 - Aug 11
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
Waterfront Oasis w/ Private Dock, 3BR/2BA
Guests can enjoy serene waterfront views from the dock.

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.4 out of 10, Exceptional, (34)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Enjoy a serene sea view from this inviting space with a wooden ceiling, glass door to a deck, and a cozy seating area.

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (179)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Sailor's Sunrise Cottage - Chesapeake Bay
Outdoor spa tub

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (49)
"Landscaping was a little lacking. We're older so the low furnishings were a little challenging, but overall; very relaxing and pretty much what we expected. "
Sailor's Sunrise Cottage - Chesapeake Bay
5-bedroom vacation home 5 minutes from historic Charlestown
Enjoy a serene lakeside retreat with a grassy area, sandy beach, and dock for boating and fishing.

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is CA $461
CA $856 total
includes taxes & fees
Aug 11 - Aug 12
5-bedroom vacation home 5 minutes from historic Charlestown
Captivating Chesapeake experience
Relax on the pier with a view of distant landforms.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (270)
"This place is the definition of the perfect getaway for a quick weekend. The home is immaculate, the scenery is beautiful and we feel instantly relaxed here. "
Captivating Chesapeake experience
* Stunning New Bungalow Perfect for Everyone *
Relax in this stylish living room with a flat-screen TV, ceiling fan, and large window.

* Stunning New Bungalow Perfect for Everyone *

9.8 out of 10, Exceptional, (100)
"This was our 2nd time staying at the property and everything was just perfect! The house is fully stocked, owners are very responsive, the home is very clean, and the beds are super comfy!"
The price is CA $206
CA $379 total
includes taxes & fees
Aug 17 - Aug 18
* Stunning New Bungalow Perfect for Everyone *
Waterfront house with amazing views. Top of the Chesapeake
Relax on the deck with Adirondack chairs and enjoy the serene lake view.

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (99)
"The water views, sunrises, and many local birds, including a nearby osprey nest, were all spectacular. The whole back of the house is a bank of windows (living room and master bedroom). It feels private as your view is just your outdoor lounge area, dock, and the water. No big downsides (minorly need space for tooth brushes as the sinks are mostly the sink bowls). Everything was clean,and comfortable. In similar off the beaten path vrbo's we've had lower cleanliness or ants, but not here! ...
Waterfront house with amazing views. Top of the Chesapeake
Luxury Waterfront Home Built for Entertaining!
Cozy attic retreat with two beds, a skylight, and a ceiling fan.

Luxury Waterfront Home Built for Entertaining!

2.0 out of 10, (1)
The price is CA $770
CA $1,248 total
includes taxes & fees
Aug 13 - Aug 14
Luxury Waterfront Home Built for Entertaining!
Dock & Hot Tub: Susquehanna River Retreat!
Relax by the fireplace in this inviting living area with a comfortable sofa and flat-screen TV.

Dock & Hot Tub: Susquehanna River Retreat!

9.2 out of 10, Wonderful, (32)
"Wonderful space, beautiful view. Only one issue that was quickly resolved. Would definitely stay there again"
Dock & Hot Tub: Susquehanna River Retreat!
River Haven with Hot Tub | 4 Bed, 3.5 Bath
Relax and socialize in this spacious outdoor deck area with comfortable seating options and lush green surroundings.

River Haven with Hot Tub | 4 Bed, 3.5 Bath

9.8 out of 10, Exceptional, (28)
"I had such a peaceful stay at John's place. The setting was incredibly tranquil, perfect for a relaxing getaway. The garden was beautiful, and I loved sipping my morning Tea on the patio. Highly recommend for anyone looking to unwind."
River Haven with Hot Tub | 4 Bed, 3.5 Bath
Quiet house heated pool & waterfall open all year
Relax by the serene pool surrounded by lush greenery and comfortable lounge seating.

Quiet house heated pool & waterfall open all year

10.0 out of 10, Exceptional, (4)
"Place was absolutely perfect. What a gem. House was wonderful and beautiful, the road in front barely had any cars go by. We had no issues with any bugs outdoors, there were plenty but didnt bother us one bit. Property owner was super sweet and helpful!! "
The price is CA $409
CA $686 total
includes taxes & fees
Aug 24 - Aug 25
Quiet house heated pool & waterfall open all year
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
Relax on the deck with a hot tub and bench, surrounded by serene lake views and lush greenery.

LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB

9.8 out of 10, Exceptional, (277)
"Absolutely love the views of the water, we had breakfast and lunch outside whenever the weather permits, and thoroughly enjoyed the peacefulness of the surroundings. Host Brian was very responsive and followed up quickly on a few of my requestsAll in all, enjoyed the stay"
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
Baseball Lovers Paradise!
Enjoy meals at the glass-top dining table surrounded by comfortable chairs.

Baseball Lovers Paradise!

8.4 out of 10, Very good, (7)
"Nice and convenient for Ripken!"
Baseball Lovers Paradise!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestnut Hill Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10/10 Excellent
"It was a great place to stop over for just the night. The area did look safe to me… staff was nice, place smelled great👍"
Lynn 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A